There are dozens of indoor and outdoor activities, attractions, and restaurants to enjoy within a few minutes of Sheffield Lodge. Whether the day is warm or cold, sunny or dark, there are destinations in the Berkshires that will keep you busy all day long no matter the season.
Things To Do Nearby
Southern Berkshire Winter and Spring Events
Sheffield Lodge is the southern gateway to the Berkshires being just north of the Connecticut border where many of the Berkshire activities happen. It’s only 100 miles north of New York City or 2 ½ hours by car, bus or train. Sheffield is a small rural town first settled in 1733 with a friendly relaxed lifestyle. It mixes rural farm country with second homes in a charming town. There are historic buildings, covered bridges, breweries, vineyards, and outdoor activities. The restaurant options are large when shared with Great Barrington the next town north. Sheffield is home to the first licensed outdoor cannabis farms with three facilities to date. Dewey Hall always has entertainment on its schedule. Sheffield is also home to several distilleries for tours and tastings, and Sheffield Pottery sells supplies and has a showroom for local potters to display their wares. Two ski resorts, Catamount and Ski Butternut are within 15 minute of the lodge making Sheffield Lodge the perfect place to stay while enjoying all these local activities and events.
Winter months, Norman Rockwell Museum, Spirit of Giving exhibit
Now – May 10, Berkshire Museum, She Shapes History
Now – Feb. 9, The Clark, Travels on Paper
Dec. 6-8, Hancock Shaker Village, Hancock Holidays
Dec. 6, 7pm Yule Jam
Dec. 7 & 8, 10am-2pm Brunch with Santa
Dec. 7, 6pm Holiday dinner
Dec. 8, 4pm & 6pm Service of Lessons & Carols
Dec. 14- Mar. 22, The Clark, Arabesque
Dec. 22, Mahaiwe Performing Arts Center, Bolshoi Ballet in HD
Dec. 28 and 30, Ventfort Hall, Marionette Performance, The Frog Prince
Dec. 30, Berkshire Museum, Last Year in America, poets share stories
Dec. 31, Berkshire Theatre Group-Colonial Theatre New Year’s Eve with Max
Dec. 31, Mahaiwe Performing Arts Center, Berkshire Bach Society: Bach at
Jan. 20, Norman Rockwell Museum, Readings from ‘How to be an Antiracist’
Jan. 18, Norman Rockwell Museum, A Place to Land: Jerry Pinkney
Jan. 18, Great Barrington Winter Farmers Market at Monument Valley
Jan. 25, Berkshire Theatre Group-Tribute to Jackson Browne
Jan. 26, Mahaiwe Performing Arts Center, Giselle
Feb. 1, St. James Place, Crescendo concert
Feb. 13, Troy Savings Bank Music Hall, Nat’l Orchestra of Ukraine
Feb. 15, Berkshire Theatre Group-Memories of Patsy Cline
February, Salisbury, CT. Jumpfest
Feb. 16, Hancock Shaker Village, The Big Chill. 11am-5pm
Feb. 22, St. James Place, Grand Piano Trios- Schubert and Brahms
Feb. 23, Mahaiwe, Swan Lake
Mar. 21, Mahawe, music of Saint-Saens, Debussy, and Faure piano quartet
Mar. 29,Mahaiwe, Romeo and Juliet
Mar. 29, St. James Place, Crescendo concert
Apr. 12, St. James Place, soprano Julianne Baird sings J.S. Bach
Apr. 25, The Mahaiwe, Skylark, Hidden Symbols, Secret Codes, A Cappella
Apr. 29, Mahaiwe, Balanchine’s Jewels
May 21, Great Barrington Winter Indoor Farmers Market
May 23, The Mahaiwe, Beethoven at 250!
Jun. 13, The Mahaiwe, Café Music-Jazz, Rap and World Premiere!
Jun. 13-16, Bethel Woods Center, Mountain Jam with Willie Nelson
Jun. 21 Tanglewood opening weekend with Judi Collins and Arlo Guthrie
Aug. 15-18, Bethel Woods Center, Carlos Santana and Ringo Starr
Aug. 15, Tanglewood, 20th anniversary of John Williams ‘Film Night’
Aug. 21, Tanglewood Boston Pops ‘Star Wars: Episode V The Empire Strikes
Things to Do
Year-round activities throughout the Berkshires. No wonder the Berkshires are so popular among visitors from all over the world. Popular outdoor activities include hiking, biking, hunting, fishing, horseback trail rides, boating, and so much more. During the summer season, visitors can enjoy a continuous schedule of cultural events such as Tanglewood music festival, Jacob’s Pillow Dance Festival, theatrical stage productions and art museums.
Covid-19 note- Tanglewood and Jacobs Pillow are closed until further notice.Read More...
Visitors can hike the public trails, visit nearby State Parks, and waterfalls, and experience the brand-new zip lines at Catamount Aerial Adventure Park.
Covid-19 note- Most outdoor recreation areas remain open. Now is a good time to get outdoors and breath the fresh air. Check the websites for particular information.
This mix of nature with fun and cultural activities, attracts families with children of all ages. There are lectures and workshops, concerts and festivals. Spring, summer, and fall are enjoyed by visitors seeking enjoyable, stress-free vacations exploring, shopping, and antiquing, or be a ‘Leaf Peeper’ in October to watch the fall colors change. The winter season attracts skiers, snowboarders and hikers to the area, and the museums are open year-round.
Wine & Dining
Throughout the Berkshires there are restaurants to suite everyone’s tastes from pizza and burger spots, farm-to-table, to exquisite fine dining destinations. We have included a few of the most popular locations for you to consider:
*Covid-19 note- Most restaurants are open for take out only, though there are now several offering dine-in options. Call ahead for information. Most all restaurants close at 9:00 each evening during the pandemic.Read More...
- Aegean Breeze – Delicious Greek fare.
- Aroma Bar & Grill – delicious Indian cuisine.
- Baba Louie’s Pizza – Wood-fired pizza, special dietary pizzas available.
- Big Elm Distillery – Tap room is a great place to visit for group trips. Free tours on Saturdays.
- Barrington Brewery & Restaurant- Ale house
- Berkshire Mountain Distillery – Take a tour through the distillery
- The Bistro Box – Small outdoor eatery with fantastic food. Closes early each day
- The Bridge Restaurant– American style comfort food
- The Egremont Barn – Pub fare and bar with live music (currently no live music).
- Fiddleheads Grill – Lunch and dinner comfort food.
- Four Brothers Pizza Inn– Good family-style Greek fare
- GB EATS – Classic American diner
- Great Barrington Bagel & Deli Co.- great bagels and topping options
- John Andrews Farmhouse Restaurant – delicious farm-to-table menus
- The Lion’s Den Pub – at Red Lion Inn Stockbridge
- Le Trois Emme Vineyard & Winery – Taste delicious hors d’oeuvre parings with each wine. Great for group visits.
- Manhattan Pizza Co
- Marketplace Café
- Mom’s Country Café – Delicious home cooking for breakfast and lunch
- The Old Mill– Weathered circa 1797 grist mill houses cozy eatery specializing in posh modern fare plus bar menu
- Prairie Whale – Home and farm food, outdoor dining
- Red Lion Dining Room- elegant, stylish cuisine
- Stagecoach Tavern – 200 year old rustic atmosphere at Racebrook Lodge, outdoor dining currently
- Starving Artist Café – Local, organic ingredients. Music on Sundays.
- Tangier Café – Moroccan-inspired dishes
You’ll find many unique places to shop in Great Barrington, Sheffield, Canaan, Lee and Stockbridge.
Covid-19 note- Some shops are now open with limited hours. Call ahead to be sure.
- Emporium Antiques
- Chelsea Antiques
- Great Barrington Antiques Center
- Berkshire Great Finds
- This & That by Habitat
- Goodwill – 6 thrift stores
- Asia Barong – The largest Asian Art Gallery in America, Definitive Museum/Gallery of Pan-Asiatic Art and Sculpture
Covid-19 note- Many shops are open with limited hours.
- Mirror, Mirror
- Zippy Chicks
- Country Living Fair
Each town has a farmers’ market. Check with each for the day it’s open. *Covid-19 note- Now open.
It is impossible to list all of the different trails, falls and scenic routes. Below is a group of the most popular nearby.
Appalachian Trail cuts 91 miles through the county and passes over Mount Greylock at 3,491 elevation. Clarksburg State Forest in the north and October Mountain State Forest at the south. Hike sections of the trail over the mountains or across the flats.
Bartholomew’s Cobble in Sheffield has spectacular views of the countryside seen from 1000 ft. high. Dogs are discouraged.
Bash Bish State Park with the longest waterfall drop in Mass. through large rock formations in a tall forest in Egremont. Perfect for a summer afternoon short hike. Wade in the shallows, picnic on the rocks. *Covid-19 update- falls are open.
Berkshire Botanical Gardens – 15 acres of cultivated gardens with an emphasis on local native plants.* Covid-19 update- Now open for walking the trails.
Blue Rider Stables – Provides a safe and nurturing environment for students of all ages. *Covid-19 note- closed until further notice.
Butternut Ski Area – Ski lessons, night skiing, passes, and packages. *Covid-19 note- closed until further notice.
Catamount Mountain Resort – Enjoy winter snow skiing and an adventure park in the summer. *Covid-19 update-Summer experiences are now open.
The Cove Bowling Alley – Bowl, parties and events, tournaments, pro-shop, leagues and clubs. *Covid-19 note- closed until further notice.
Fly the Berkshires – Provides maintenance, flight instruction and scenic flights. Home to private and business-owned general aviation aircraft. *Covid-19 note- closed until further notice.
Hancock Shaker Village – Go back in time at this living history museum. *Covid-19 update- Now open for visitors with compliance requirements.
Housatonic River Walk – Downtown Great Barrington. Enjoy a leisurely stroll through nature along the river.
The Kilpatrick Athletic Center – A fitness center featuring aerobics and dance studio, jogging track, pool, rock climbing wall racquetball, tennis and basketball courts. *Covid-19 update-Now open for visitors with compliance requirements.
Lake Garfield – A public beach located in Monterey, MA with lifeguards on duty during summer season. Swimming lessons, and boating available by contacting the parks department.
Lake Mansfield – Has sandy beaches, picnic area, and swimming with lifeguard during summer season in Great Barrington, MA.
Lime Kiln Farm Wildlife Sanctuary – Hike trails, enjoy vistas, look for wildlife, learn about plant communities.
Mount Greylock – At 3500 ft. high, this area offers breathtaking views. Try a challenging hike to the summit. Set up camp and stay on the mountain overnight and experience the awe-inspiring beauty above. Visitor Center: 30 Rockwell Road, Lanesborough
Monument Mountain – North Great Barrington. Moderate level hike to summit for magnificent views. *Covid-19 update- Now open during daylight hours.
Naumkeag – An elegant estate known for its gardens and rare Berkshire “cottage.”
Race Brook Falls – On Route 41 (1/2 mile south of the Sheffield Lodge). Moderate exercise hike. Best in spring during snowmelt.
Umpachene Falls (and nearby Campbell Falls) – Enjoy a picnic lunch on the beach. Great for children and dogs.
The Barn, Bar and Pub – Live music, burgers, Karaoke and comedy night. Intimate rustic setting, delicious food and great acoustics. *Covid-19 note- closed until further notice.
The Guthrie Center – In Great Barrington’s Trinity Church. A home of interfaith services, spiritual exchange and music. *Covid-19 note- closed until further notice.
Falcon Ridge Folk Festival – This great event is in its 31st year of folk music and dance. *Covid-19 note- closed until further notice.Read More...
Jacobs Pillow Dance Festival – Regarded as the dance center and destination of the nation, it is a national Historic Landmark hosting the longest-running international dance festival. Over 160 performances each season of emerging artists and world legends. They house a most prestigious dance training center in the country. Runs from mid-June through August. *Covid-19 note- closed until further notice.
Mahaiwe Performing Arts Center – Offers music, dance, theater, opera, movies and family programs. *Covid-19 note- closed until further notice.
Berkshire Choral Festival – Held for 4 weeks at the Berkshire School. Gives choral singers the opportunity to rehearse and perform masterpieces of choral repertoire under world-class conductors and staff. *Covid-19 note- closed until further notice.
Tanglewood Music Festival – Founded in 1982, the main local attraction as the summer home of the Boston Symphony Orchestra is one of the most renowned musical arts venues in the region. Special invites to some of the most talented and widely acclaimed musical artists and acts. *Covid-19 note- closed until further notice.
Tannery Pond Concerts – In New Lebanon, NY. A destination for impressive classical music talent. Sit on beautifully crafted Shaker benches. Now, the private preparatory school for 180 students. Beware, the hall is not air conditioned. *Covid-19 note- closed until further notice.
Williamstown Theatre Festival – Classic plays with fresh productions as well as new plays and musicals. *Covid-19 note- closed until further notice.
Museums & Galleries
Berkshire Museum of Art Science & History – Family oriented to spark creativity and innovative thinking by making inspirational and educational connections. Filled with natural history and ancient civilization located in Pittsfield, MA. *Covid-19 note- closed until further notice.
Clark Art Institute – An art museum and research institution located in Williamstown, MA. *Covid-19 note- Call for hours.
Hancock Shaker Village – A world of rural living designed Hancock Shaker Village est. 1791. Closed and reopened as a museum and is still a working farm. *Covid-19 note- closed until further notice.
Mass MoCA Museum of Contemporary Art – Located in North Adams and also one of the top music venues. *Covid-19 note- Call for hours.Read More...
Naumkeag and The Mount built in the Guilded Age – See how the elites spent their times in the county see the splendors of the house gardens. Walk through exquisite gardens and fountain pools showing domestic beauty. Enjoy the Daffodil Festival and the Tulip festival here as well. *Covid-19 note- closed until further notice.
Norman Rockwell Museum – Dedicated to education and art appreciation inspired by Rockwell’s undeniable legacy on American Art and more. *Covid-19 note- closed until further notice.
Schantz Galleries – Located in Stockbridge and known for its glass artist works. *Covid-19 note- closed until further notice.
Williams College Museum of Art & Sculpture – Offers the opportunity to encounter painting. *Covid-19 note- closed until further notice. and sculpture firsthand. The Rose Gallery is a state of the art classroom committed to enhancing undergraduate education.
Berkshire Theatre Group – One of the largest arts organization in the area with 5 stages in the county. Including Fitzpatrick Main Stage, Unicorn Theatre, Neil Ellenoff Stage, all in Stockbridge and the Colonial Theatre and the Garage in Pittsfield. *Covid-19 note- Closed until further notice.
Barrington Stage Company – Award winning Theater in the Berkshires presenting musicals, drama, and original productions. *Covid-19 note- Closed until further notice.
The Colonial Theater – Part of the Berkshire Theatre Festival. *Covid-19 note- Closed until further notice.Read More...
Mahaiwe Theater – One of the oldest surviving theaters with great acoustics. Open year round and boasts a performing arts center with self-selected programs of incredibly varied selection of musical performances from family events, rock and pop shows musicals and operas. *Covid-19 note- Closed until further notice.
Shakespeare and Company – Performs Shakespeare and new plays of “social and political significance”. Conducts training programs for professional classical actors and students. *Covid-19 note- Closed until further notice.
Sosnoff Theater at Bard College – An intimate theater with an orchestra, parterre, and 2 balcony sections, and an acoustical shell that turns the theater into a concert hall for performances of chamber and symphonic music. *Covid-19 note- Closed until further notice.
Bartholomews Cobble – 6.2 miles of trails for moderate hikers. Beautiful vistas. Trails are open and great for walking in open fresh air.
Big Elm Distillery – Tap room to visit for group trips. Free tours on Saturdays. *Covid-19 note-Call for hours.
Berkshire Mountain Distillery – Take a tour through the distillery. *Covid-19 note-Call for hours.
Colonel John Ashley House – Learn about Elizabeth ‘Mumbet’ Freeman, a black enslaved woman who sued for and won her freedom. Is closed for summer of 2020.Read More...
Le Trois Emme Vineyard & Winery – Taste delicious hors d’oeuvre parings with each wine. Great for group visits. *Covid-19 note-Call for hours.
Sheffield Covered Bridge – Oldest covered bridge in Massachusetts before it burned in 1994. *Covid-19 note-Good outdoor space for walking and enjoying fresh air. See the UFO marker on back side of bridge.
Sheffield Pottery – Premium quality equipment, supplies, products, service, and dependability. *Covid-19 note-Call for hours.
Thom Reed UFO Monument – At Sheffield Covered Bridge. Easy walk from parking. *Covid-19 note- Good outdoor space for walking and enjoying fresh air.
Woodstock – Take a day trip to Woodstock, a town of rural beauty. A walking and shopping town, and still has the fun and funky feeling with artsy shops.